RVP, Enterprise Sales

About Us

Observe.AI is the leading AI agent platform for customer experience. It enables enterprises to deploy AI agents that automate customer interactions, delivering natural conversations for customers with predictable outcomes for the business.

Observe.AI combines advanced speech understanding, workflow automation, and enterprise-grade governance to execute end-to-end workflows with AI agents. It also enables teams to guide and augment human agents with AI copilots, and analyze 100% of human and AI interactions for insights, coaching, and quality management.

Companies like DoorDash, Affordable Care, Signify Health, and Verida use Observe.AI to transform customer experiences every day by accelerating service speed, increasing operational efficiency, and strengthening customer loyalty across every channel.

The Opportunity

We are hiring a Regional Vice President, Enterprise Sales to build and lead our outbound-led sales motion. The RVP, Enterprise Sales will be at the forefront of driving new logo growth and engaging C-level executives across industries. This is a hunter-first, player-coach role ideal for a high-energy leader who thrives in whitespace, has a track record of outbound pipeline generation, and is ready to build and lead a high-performing team. You’ll be accountable for owning pipeline generation, closing new logos, and building the people, processes, and playbook to scale outbound-led revenue growth in the enterprise segment. If you thrive in high-growth environments and are passionate about translating GenAI innovation into measurable customer outcomes, and shaping the future of customer experience - this role is for you. 

What you’ll be doing

Hunter Mentality & Outbound Strategy

• Own and execute an outbound-first GTM motion targeting mid-market and enterprise accounts (typically <500 agents)
• Build and refine ICPs, persona-based messaging, outbound cadences, and prospecting strategies to drive predictable top-of-funnel activity.
• Collaborate with marketing and SDR teams to align on high-converting campaigns.

Player-Coach Sales Leadership

• Lead from the front as a quota-carrying seller, personally prospecting, engaging, and closing deals.
• Hire, train, and coach a team of Mid-Market AEs, setting the tone for a metrics-driven, outbound culture.
• Instill discipline around outbound KPIs—activities, pipeline coverage, conversion rates—while celebrating grit and curiosity.

Build & Scale the Function

• Design the team structure, territories, compensation, hiring plan, and onboarding for an outbound-led mid-market motion.
• Establish CRM best practices, forecasting cadences, pipeline review rituals, and enablement workflows.
• Partner with RevOps, Product Marketing, and Enablement to iterate quickly based on data and feedback.

Ai/Genai Fluency

• Understand and position the value of GenAI-powered solutions in contact center, CX, and revenue acceleration workflows.
• Translate technical capabilities into business outcomes tailored for mid-market buyers across ops, support, and IT.
• Stay ahead of GenAI trends, competitors, and evolving use cases in the customer engagement space.

What you bring to the role

• 8–10+ years of B2B SaaS sales experience, including 3+ years in leadership managing mid-market or SMB teams.
• Strong track record of net-new logo acquisition via outbound prospecting—personally and as a team leader.
• Experience as a player-coach, balancing individual contributor responsibilities with team leadership.
• Comfort building from scratch—people, processes, sales motions, and culture—in a high-growth or startup environment.
• Familiarity with sales methodologies like MEDDIC, CCS, or Challenger, and tools like Salesforce, Outreach/Salesloft, Clari, Gong.
• Strong storytelling and discovery skills; able to earn trust with technical and business stakeholders alike.

Preferred Background

• Deep familiarity with GenAI, NLP, LLMs, or ML applications in enterprise use cases.
• Global or multi-regional sales leadership experience (North America, EMEA, or APAC).
• Background in building high-performing sales teams at companies in post-Series B to pre-IPO stages.
• Bachelor's or Master’s degree in Business, Engineering, or a related technical discipline.

Our Commitment to Inclusion and Belonging

Observe.AI is an Equal Employment Opportunity employer that proudly pursues and hires a diverse workforce. Observe AI does not make hiring or employment decisions on the basis of race, color, religion or religious belief, ethnic or national origin, nationality, sex, gender, gender identity, sexual orientation, disability, age, military or veteran status, or any other basis protected by applicable local, state, or federal laws or prohibited by Company policy. Observe.AI also strives for a healthy and safe workplace and strictly prohibits harassment of any kind.

We welcome all people. We celebrate diversity of all kinds and are committed to creating an inclusive culture built on a foundation of respect for all individuals. We seek to hire, develop, and retain talented people from all backgrounds. Individuals from non-traditional backgrounds, historically marginalized or underrepresented groups are strongly encouraged to apply.

If you are ambitious, make an impact wherever you go, and you're ready to shape the future of Observe.AI, we encourage you to apply. For more information, visit www.observe.ai.